The first reaction would have been 'no' given that the Redente six-year-old didn't have much Polytrack form – a debut third and a recent unplaced finish - but thinking out of the square, the Australian horseman thought 'why not'.
Fitzsimmons, who took over Gold Star 's training and a few other Gold Stable wards after his mentor Cliff Brown returned to Australia in March, did get one win on turf from the previous four-time turf winner, but a couple of months ago, he decided to revisit the Polytrack route with an eye on the Merlion Trophy two months later on November 27.
The gamble paid off. Donning blinkers for the first time, Gold Star came from near-last to storm home in a Class 2 race over the Polytrack 1200m.
Two more outings on grass produced a close second to top sprinter Makkem Lad in a Kranji Stakes A (1200m) and a luckless seventh (only 2 ½ lengths behind) to Kharisma in a Class 1 (1200m) two weeks ago, but Fitzsimmons has already set his mind on Singapore's only Polytrack feature left on this season's calendar as his grand final.
"We always thought he could win a Group race. Long range, I thought if I could get him to win on Poly, the Merlion Trophy would sort of be his race," said Fitzsimmons, who, in contrast to his first two muted seasons, has enjoyed an outstanding third year with 32 winners and a fourth place on the leaderboard, but has yet to open his Group race account.
"The blinkers helped him in that race as well. We could then move to the next step.
"He's also in a rich vein of form. His second in the Kranji Stakes A was really good, and I feel he shouldn't have missed a place at his last start.
"I thought that was his race, but he didn't get a great deal of luck that day. If he had come to the outside as I wanted, he could have finished really close.
"Anyway, he has pulled up good and he gets his chance in a Group race this week. That'd be amazing if he could give me my first Group win, especially for the Yong family, who has been a great supporter of mine from Day 1."
Gold Star will again be ridden by Wong Chin Chuen even if Fitzsimmons thought the former two-time Singapore champion apprentice jockey didn't turn in his best ride at their last pairing.
"Jimmy knows the horse. He asked for the ride, and I decided to stick with him," he said.
"Let's hope he gets a bit more luck in the running this time."
Gold Star has drawn barrier six and will face sprinting stalwarts like Grand Koonta, Fame Star and Nowyousee as well as his last-start victor Kharisma, but under sufferance in relation to the change in handicapping conditions.
Kharisma gave him five kilos away at their last encounter for a two-and-a-half-length beating, but they are now pegged back on level terms.
"Last time was a weight-for-age race, but they are now at level weights, which makes it more difficult for him," said Fitzsimmons.
"But he's pulled up good since and has been working well. Fingers crossed he goes all right."